ChemInform Abstract: Property-Guided Synthesis of Aza-Tricyclic Indolines: Development of Gold Catalysis en route.

ChemInform ◽  
2016 ◽  
Vol 47 (36) ◽  
Author(s):  
Patrick M. Barbour ◽  
Wei Wang ◽  
Le Chang ◽  
Kasey L. Pickard ◽  
Rana Rais ◽  
...  
2018 ◽  
Author(s):  
Victor Laserna ◽  
Tom Sheppard

A versatile approach to the valorization of propargylic alcohols is reported, enabling controlled access to three different products from the same starting materials. Firstly, a general method for the hydroamination of propargylic alcohols with anilines is described using gold catalysis to give 3-hydroxy imines with complete regioselectivity. These 3-hydroxyimines can be reduced to give 1,3-aminoalcohols with high syn seletivity. Alternatively, by using a catalytic quantity of aniline, 3-hydroxyketones can be obtained in high yield directly from propargylic alcohols. Further manipulation of the reaction conditions enables the selective formation of 3-aminoketones via a rearrangement/hydroamination pathway.<br>


Author(s):  
Philipp Stein ◽  
Matthias Rudolph ◽  
A. Stephen K. Hashmi
Keyword(s):  

2011 ◽  
Vol 7 ◽  
pp. 570-577 ◽  
Author(s):  
Sami F Tlais ◽  
Gregory B Dudley

A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catalysis in the activation of alkyne π-systems.


2007 ◽  
pp. 333-346 ◽  
Author(s):  
Eloísa Jiménez-Núñez ◽  
Antonio M. Echavarren

2021 ◽  
Author(s):  
Chetan C. Chintawar ◽  
Amit K. Yadav ◽  
Anil Kumar ◽  
Shashank P. Sancheti ◽  
Nitin T. Patil

ChemInform ◽  
2015 ◽  
Vol 46 (5) ◽  
pp. no-no
Author(s):  
Shigekazu Ito ◽  
Masaki Nanko ◽  
Koichi Mikami
Keyword(s):  

2013 ◽  
Vol 52 (50) ◽  
pp. 13146-13148 ◽  
Author(s):  
Rafael Gramage-Doria ◽  
Joost N. H. Reek
Keyword(s):  

2013 ◽  
Vol 2013 (28) ◽  
pp. 6267-6279 ◽  
Author(s):  
Valentina Pirovano ◽  
Monica Dell'Acqua ◽  
Diego Facoetti ◽  
Donatella Nava ◽  
Silvia Rizzato ◽  
...  

2012 ◽  
Vol 31 (8) ◽  
pp. 3074-3080 ◽  
Author(s):  
Gloria Mazzone ◽  
Nino Russo ◽  
Emilia Sicilia
Keyword(s):  

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